Bromine → HCID 66825035, compound

HRID 1423096Notes

Reaction equation

HRID 1423096 reaction equation
[CH:1]1([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:14]Br>C(Cl)Cl>[Br:14][C:11]1[CH:10]=[CH:9][C:8]([OH:13])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:12]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 43143456HCID 43143456, compound

Product 1

HCID 66825035HCID 66825035, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(cyclopentyloxy)phenol intermediate (5.6 g, 31 mmol) in CH2Cl2 (40 mL) at −78° C. was treated dropwise with a solution of bromine (4.9 g, 31 mmol) in CH2Cl2 (10 mL) via addition funnel over a 1 h period. After warming up to room temperature gradually over 3 h, the reaction was quenched by addition of a saturated aqueous solution of Na2S2O4. The isolated organic layer was washed with water, brine, dried over Na2SO4, filtered, and concentrated. The crude mixture was then purified by ISCO (0-10% EtOAc in hexanes) to afford intermediate 4-bromo-2-(cyclopentyloxy)phenol (2.6 g, 32%) as colorless oil. 1H NMR (300 MHz, CDCl3) 6.97-6.93 (m, 2H), 6.78 (d, J=9.3, 1H), 5.54 (s, 1H), 4.78 (m, 1H), 1.95-1.63 (m, 8H).

Workup

  1. customthe reaction was quenched by addition of a saturated aqueous solution of Na2S2O4
  2. washThe isolated organic layer was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude mixture was then purified by ISCO (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8c103e314024442191b1769e95eab9a4
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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